| Triflic acid-catalyzed additions of 2-alkoxycarbonyl allylboronates to aldehydes. Study of scope and mechanistic investigation of the reaction stereochemistry. | |
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MedLine Citation:
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PMID: 17288375 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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The substrate scope and the effect of substrate on the observed inversion of stereoselectivity in the triflic acid-catalyzed allylboration reaction between 2-alkoxycarbonyl allylboronates and aldehydes are presented. A mechanistic investigation is described so as to confirm the involvement of a carbocation intermediate as the source of stereochemical inversion. This methodology allows a facile access to beta,gamma-disubstituted five-membered ring lactones with an exo-methylene at the alpha-position. |
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Authors:
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Tim G Elford; Yuichiro Arimura; Siu Hong Yu; Dennis G Hall |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Feb |
Date Detail:
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Created Date: 2007-02-09 Completed Date: 2007-04-17 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 1276-84 Citation Subset: - |
Affiliation:
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Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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